Lewis acid mediated asymmetric [2, 3]-sigmatropic rearrangement of allylic amines. Scope and mechanistic investigation

…, O Panknin, P Tuzina, P Somfai

文献索引：Blid, Jan; Panknin, Olaf; Tuzina, Pavel; Somfai, Peter Journal of Organic Chemistry, 2007 , vol. 72, # 4 p. 1294 - 1300

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被引用次数: 23

摘要

The first asymmetric [2, 3]-sigmatropic rearrangement of achiral allylic amines has been realized by quaternization of the amines with an enantiomerically pure diazaborolidine and subsequent treatment with Et3N. The resultant homoallylic amines were obtained in good yields and excellent ee's. The observed diastereo-and enantioselectivities were rationalized by invoking a kinetically controlled process, and support for this model was obtained from ...